Cheap Flights From Cleveland, Ohio (CLE) To Chicago, Illinois (MDW)

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Fares from Cleveland, OH (CLE)
$186 RT to
Chicago, IL (MDW)
Sorry this deal is over or has been sold out! But here’s another great Airfarewatchdog verified fare for this route!
$186 RT Cleveland to Chicago, IL
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Airline(s)
Southwest
Seats:
Seats are not available on all flights or all dates of travel. You may need to have flexible travel dates to find this fare. Fares for travel on holidays may be higher.
Available:
Tue/Wed/Sat
Travel Starting:
Friday, 28 August 2015
Travel Ending:
Wednesday, 28 October 2015
Purchase By:
Thursday, 07 May 2015
More Details:
No min. stay., Fare can be bought one-way for half the lowest roundtrip price., Late Summer/Fall travel; Nonstop flights.
Last Updated:
Tuesday, 28 April 2015
Our Notes:
Travel August 28 through October 28, 2015. Blackout Dates Apply: September 5, 2015 This is a fare from Southwest, please visit Southwest.com to find this fare. Other airlines often match Southwest sales, so search other sites to find the best option.
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All mandatory taxes/fees are included in the price. Tax-inclusive fare may be a few dollars higher or lower depending on the airport you connect through, if any. Baggage fees, if applicable, and other optional fees are not included.

Our Dealhounds found this airfare using flexible date search. This means we searched a range of dates to find you the best price.

More Flights From Cleveland To Chicago (CLE-MDW)

Price
Details
$186 RT No min. stay.. Fare can be bought one-way for half the lowest roundtrip... (Southwest) See all details »
  • Airline(s):
    Southwest
  • Seats are:
    Seats Are Not Available On All Flights Or All Dates Of Travel. You May Need To Have Flexible Travel Dates To Find This Fare. Fares For Travel On Holidays May Be Higher.
  • Available for travel:
    Tue/Wed/Sat
  • Travel starting:
    Friday, 28 August 2015
  • Travel ending:
    Wednesday, October 28, 2015
  • More Details:
    No Min. Stay., Fare Can Be Bought One-way For Half The Lowest Roundtrip Price., Late Summer/Fall Travel; Nonstop Flights.
  • Last Updated:
    Tuesday, April 28, 2015
  • Our Notes:
    Travel August 28 through October 28, 2015. Blackout Dates Apply: September 5, 2015 This is a fare from Southwest, please visit Southwest.com to find this ...morefare. Other airlines often match Southwest sales, so search other sites to find the best option.
$188 RT Non-Stop Flights.. Travel period valid through October.. No min. stay..... (Southwest) See all details »
  • Airline(s):
    Southwest
  • Seats are:
    Seats Are Not Available On All Flights Or All Dates Of Travel. You May Need To Have Flexible Travel Dates To Find This Fare. Fares For Travel On Holidays May Be Higher.
  • Advance Purchase:
    21 Days
  • Available for travel:
    7 Days/week, If Available
  • Travel ending:
    Friday, October 30, 2015
  • More Details:
    Non-Stop Flights., Travel Period Valid Through October., No Min. Stay., Fare Can Be Bought One-way For Half The Lowest Roundtrip Price.
  • Last Updated:
    Monday, April 27, 2015
  • Our Notes:
    This is a fare from Southwest. Visit Southwest.com to find this fare. Other airlines often match Southwest sales, so search other sites to find your best ...moreoption.
$204 RT No min. stay.. Travel period valid through October. (Delta) See all details »
  • Airline(s):
    Delta
  • Seats are:
    Seats Are Not Available On All Flights Or All Dates Of Travel. You May Need To Have Flexible Travel Dates To Find This Fare. Fares For Travel On Holidays May Be Higher.
  • Advance Purchase:
    21 Days
  • Available for travel:
    Mon-Sat
  • More Details:
    No Min. Stay., Travel Period Valid Through October.
  • Last Updated:
    Monday, April 27, 2015
  • Our Notes:
    Tue/Wed Travel Some Weeks Between June And August.

Reviews for Cleveland to Chicago (CLE-MDW)

based on 2 reviews
Flown this route before? Write a review
    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    New boarding procedures

    by eharbart on September 9, 2010

    Flight from Cleveland to Chicago

    Airline:
    Southwest
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    September 2010
    Seat Class:
    economy

    I really like the numbered positions for boarding now. It seems alot easier and fair in their boarding process. It helps the passinger's not having to stand in line to get a good position and since we are in our 70's it is very important not to have to stand a long time. It was also very fast.

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    comfortable seats, on time , good value

    by orchardview on August 17, 2010

    Flight from Cleveland to Chicago

    Airline:
    Southwest
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    August 2010
    Seat Class:
    economy

    It was a bit bumpy but the seats were comfortable if not too wide the open seating was interesting I got to sit with my friends both ways but sat far back than usual. Boarding was quick and orderly same for deplaning

    I would fly them again this was my first experience. My suitcase was mashed both ways broke the mirror in my cosmetic bag lid and broke the ridged in side corner of my soft luggage. Every seat full both ways.

Flown this route before? Write a review
Sample Fares found by other travelers within the past 72 hours
Price From/To Depart/Return Airline
$400 Flight from Cleveland to Midway (CLE-MDW) Mon, Jun 16 - Wed, Jun 18 Delta Air Lines
$425 Flight from Cleveland to Midway (CLE-MDW) Wed, Jun 11 - Wed, Jun 25 Delta Air Lines
$543 Flight from Cleveland to Midway (CLE-MDW) Fri, Jun 6 - Sat, Jun 7 Delta Air Lines
$553 Flight from Cleveland to Midway (CLE-MDW) Fri, Jun 6 - Mon, Jun 9 Delta Air Lines
$630 Flight from Cleveland to Midway (CLE-MDW) Wed, Jun 11 - Fri, Jun 13 Delta Air Lines
$655 Flight from Cleveland to Midway (CLE-MDW) Fri, Jun 13 - Mon, Jun 16 Delta Air Lines
$660 Flight from Cleveland to Midway (CLE-MDW) Mon, Jun 16 - Mon, Jun 16 Delta Air Lines
$714 Flight from Cleveland to Midway (CLE-MDW) Wed, Jun 11 - Thu, Jun 19 Delta Air Lines
$745 Flight from Cleveland to Midway (CLE-MDW) Sun, Jun 8 - Wed, Jun 11 Delta Air Lines
$755 Flight from Cleveland to Midway (CLE-MDW) Fri, Jun 6 - Sun, Jun 8 Delta Air Lines
There are approximately 12 flights covering the route from Hopkins International Airport in Cleveland to Midway Airport in Chicago, provided by as many as 2 airlines.

The following airlines sometimes offer nonstop cheap flights from Cleveland to Chicago:

Transwest Air

As an alternative to flying from Cleveland, you may also want to try searching for cheap flights from Erie (ERI).
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